Charlie Sheen’s Highs and Lows

Published December 29, 2009•Updated on October 28, 2011 at 12:00 am

He was one of the highest paid TV actors, but he's had a rocky road.

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FilmMagic
Charlie Sheen's sitcom is homeless no longer! FX says it has acquired "Anger Management," a show based on the 2003 Adam Sandler-Jack Nicholson flick. The show will air in summer 2012. Click to see more of Charlie Sheen's highs and lows.

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AP
Charlie Sheen's decision to make nice with his former colleagues paid off. He scored a cool $25 million from settling a $100 million wrongful termination suit with Warner Bros. TV and Chuck Lorre, his former "Two and a Half Men" boss.

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WireImage
Charlie Sheen was #winning when Comedy Central's The Roast of Charlie Sheen aired the same night as the premiere of the new season of Two and a Half Men. He tweeted, “Thank you @comedycentral..! I'm moved... speechless and grateful! (and glad it's over...) Well done my friends. Well done!” after receiving about 400,000 tweets throughout the night.

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AP
Before presenting an Emmy for outstanding lead actor in a comedy, Sheen took a moment to address the cast and crew of "Two and a Half Men." Sheen said he wished them "nothing but the best for this upcoming season."

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Lionsgate Television Group President Kevin Beggs confirmed that a TV version of the Jack Nicholson/Adam Sandler movie "Anger Management" starring the warlock himself is in the works. “I chose 'Anger Management' because, while it might be a big stretch for me to play a guy with serious anger management issues, I think it is a great concept,” joked Sheen.

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And then there were none. Charlie Sheen's remaining goddess, model Natalie Kenly, has flown the Korner, leaving the warlock alone in his L.A. home. "He's not in one of the best places right now, things are very tense," an insider told Us Weekly. "It has nothing to do with her, [the relationship] just ran its course."

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After news broke Ashton Kutcher would replace Charlie Sheen on “Two and a Half Men," the Vatican Warlock Assassin predicted his old show would tank. “Enjoy seeing a 2.0 in the demo every Monday, WB," he told TMZ. "Enjoy planet Chuck, Ashton. There is no air, laughter, loyalty, or love there."

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While Sheen didn’t mince words about his old boss, Chuck Lorre, he kept it collegial with Ashton. “Kutcher is a sweetheart and a brilliant comedic performer ... Oh wait, so am I!" Sheen told TMZ.

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Getty
At last: Charlie Sheen released his song, "Winning" (of course) that was recorded with help from rapper Snoop Dogg. Sheen's live show, "Violent Torpedo of Truth," has increasingly been losing steam with viewers. Will the song reignite the craze?

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AP
Charlie Sheen is down a goddess, but that didn't stop him from having some fun at a Florida Marlins vs. Colorado Rockies baseball game. During a "Violent Torpedo of Truth" show in Florida, the actor told the audience that Rachel “Bree” Olson broke up with him through a text message.

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Sheen had a show in D.C. the same day he had a court hearing. The crowd was rowdy, and Sheen said he hated ex-wives, after he lost sole-custody of his kids. When asked how he'd handle Libyan dictator Moammar Khaddafy, Sheen replied, "I'd make him marry [my ex-wives] Brook and Denise."

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The day of his D.C. show, Sheen was battling for custody of his twin boys from his ex Brooke Mueller. While Sheen avoided the cameras, Mueller wasn't so fortunate. Sheen showed up 67 minutes late to his "Torpedo of Truth" tour.

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Sheen announced that he is organizing a bipolar awareness walk in Toronto. He asked fans to meet him at the Ritz to walk with him to Massey Hall, where he will perform Friday night. "I'm matching all donations $ for $," the Warlock tweeted. Bipolar? We thought it was #biwinning.

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Charlie Sheen should change his catchphrase to #losing. Bostonians bailed on the Warlock during the second half of his Beantown show this week. Even a cameo from "Jersey Shore" cast member Pauly D couldn't save Sheen, who shouted to fans, "Wait, don’t leave! I’m not done!”

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The Warlock had both hot-and-cold reception in New York. After the Radio City debacle, Sheen was met with a moderate bit of success. "I don't even think I was here Friday night," Sheen said of his first New York show.

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As he's prone to do, Sheen went shirtless onstage during his second New York show. We're guessing this isn't exactly a spiritual moment.

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2011
The Charlie Sheen Media Express steamrolled into New York City this weekend, and unfortunately for the troubled actor, his "Violent Torpedo of Truth/Defeat" performance at Radio City Music Hall Friday night was met with the same tepid audience response.

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Not even wearing a Yankee cap could have saved him. As NBCNewYork.com reported, the actor was heckled at 20 minutes into the Radio City show—some people shouted “boring” and “you suck.” Audience member Massimo Didonna said: "That was the biggest waste of $280 I've ever spent in my life."

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Following his smashing performance at Radio City Music Hall, Sheen took some time to hang out with another fellow bad boy, Ronnie Magro of “Jersey Shore,” in Carlstadt, NJ.

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Sheen knew his audience in Cleveland and catered to the boisterous bunch during his "Violent Torpedo of Truth" tour. The actor appeared onstage in a Cleveland Indians jersey, embellished with “Vaughn” across the back. Sheen's portrayal of the wild pitcher in the baseball movie “Major League.” landed him a standing O.

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AP
Sheen's cross country tour had a rocky start , "Violent Torpedo of Truth/Defeat Is Not an Option" bombed in Detroit but was a hit in Chicago.

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ASSOCIATED PRESS
Sheen and his so-called goddesses kicked off the month-long, 20-city variety show tour, with a sold-out show in Detroit. But the show was not what the crowd expected. CNN said Sheen showed clips of movies with no context, and continually insulted audience members and the Motor City itself.

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Tiger blood devotees in Detroit who started the night with a standing ovation ended it by cutting out early. A patron of Sheen's show at the Fox Theatre showed her displeasure following the performance where Sheen walked off the stage early after being booed throughout his performance.

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ASSOCIATED PRESS
Sheen tweaked his act for his Chicago audience, this time skipping the opening act and addressing the audience with a letter. Here, the 45-year-old former "Two and a Half Men" star looks towards a projection image of the show during his performance promising "the real story."

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With two cities down Sheen and his goddesses, Bree Olson and Natalie Kenly celebrate at the official Charlie Sheen After Party. The tour will make stops in 17 more cities including New York, Atlantic City, Dallas, and San Francisco.

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Sheen's public downfall is made more troubling with a recent youtube video "Charlie Sheen: The Unedited Version." In Sheen's self-parody of his self-destructive "20-20" interview, there's a hint the actor realizes what a joke he's become. He delivers goofy variations on his bizarre "tiger blood" and "Adonis DNA" catchphrases.

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'Duh, Winning,' 'Tiger Blood,' the actor applied to trademark 22 of his catchphrases. Records show Hyro-gliff, a California company formed last month, filed trademark applications between March 19 and 22 reports the NY Daily News. Sheen's attorney also applied to trademark Sheen's name and signature, as well as his nicknames for his home (Sober Valley Lodge) and his girlfriends (Sheen's Goddesses.)

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Charlie Sheen stormed onto the stage of Jimmy Kimmel's show in a surprise appearance, stunning the late night host with a big smacker.

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Twitter
Winning! In the latest Charlie Sheen's merchandising ploy (aside from Tiger Blood!), Sheen debuts a T-shirt that states the obvious. Duh.

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WireImage
Don't you forget about Sheen. The wacky warlock announced he will play a pair of live shows next month. The shows are being billed as "Charlie Sheen LIVE: My Violent Torpedo of Truth." Sheen, who first announced the road show on March 8, explained his intentions, "This IS where you will hear the REAL story from the Warlock. Bring it. I dare you to keep up with me."

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Hours after cops searched Charlie Sheen's home for weapons, he and soon-to-be ex-wife Brooke Mueller reached a deal for custody of their twin boys. Sheen told PopEater that he doesn't want any more children. "I can't seem to keep the ones I already have," Sheen said.

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On March 11 the lawyers of both Brooke and Charlie reached an agreement over the custody of the ex-couple's twin boys after a marathon of meetings. The agreement also nullified the restraining order that would have kept Charlie away from his ex and kids.

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On the night of March 10, the LA Police Department searched Charlie Sheen's house for possession of weapons. They found one gun and a few bullets, but the next morning Sheen tweeted: "the LAPD were AWESOME. Absolute pros! they can protect and serve this Warlock anytime!!!" later adding, "50 cops in my home. they all left. I'm still here. WINNING? 24/7."

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Sheen's next battle against the corporate trolls is a live tour he's calling "Charlie Sheen LIVE: My Violent Torpedo of Truth." Tickets go on sale March 12. "I'm going on the road," he announced, "Bring it. I dare you to keep up with me."

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Along with his live tour, the currently unemployed Sheen is toying with other business prospects - including a deal with Ad.ly to endorse products on Twitter (he could make $1 million in a year, according to Ad.ly's CEO). The sum is half the amount he made per episode on "Two and a Half Men."

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The $1 million he could make per year is also diddly-squat compared to his expenses, which include child support for 4 kids, a $7.5 million Beverly Hills mansion, and his collection of stylish cars.

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Sheen dropped another bombshell on Thursday, March 10, when he announced his plans to sue Warner Bros. and Chuck Lorre, the creator of "Two And A Half Men," for $100 million. The suit claims Sheen has “suffered the intangible loss of employment-related opportunities," due to show's decision to cut Sheen.

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Charlie Sheen was shown drinking his "tiger blood" on the roof of a Los Angeles parking garage. His "tiger blood" is, in fact, pureed mangosteen juice, marketed under the name XANGO. The company claims that the juice may help support the body's immune system.

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Sheen called the KEARTH 101 radio show on Tuesday, March 9, to offer an apology to his former co-star, Jon Cryer, labeling him a "troll," saying, "I was in a mood." He also took the call as an opportunity to endorse Rob Lowe as his sitcom substitute. "I hope he does it and kicks its a** because you know I still get pizayed," said Sheen.

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AP
Sheen may finally be coming to grips with his apparent self-destruction. In an exclusive interview with Life & Style, Sheen admits that his "winning" ways may not be as glorious as he makes them out to be. "I'm really starting to lose my mind," Sheen tells Life & Style. "I'm really trying to contain myself right now," he says. "My lawyer wants to come over to my house and take the bullets out of my gun."

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Sheen's Internet tirades and machete-wielding publicity stunts have pushed him to become the fastest celebrity ever to reach one million followers on Twitter. But Sheen can't manage the media attention himself. More than 74,000 people have applied for a social media internship with Sheen. In a fitting touch, the application asked applicants to answer "Why should you get the job?" in 75 words or less.

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The newly fired "Two And A Half Men" star lashed out at his former co-star, Jon Cryer, labeling him a "troll" and "turncoat" for failing to pick up the phone after Sheen was canned from CBS' top-rated sitcom. "Like I said: You're with me, or you're with the trolls," Sheen told E! News.

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MMI
Hours earlier, Sheen told Jeff Rossen of NBC's "Today" show that despite his firing, everything was going according to his own plan. "I didn't like that show anyway or those dumb bowling shirts they made me wear," he told Rossen. "Now I'm free." Later, he was spotted in Hollywood brandishing a machete while one of his "goddesses," Natalie Kenly, looked on.

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FilmMagic
CBS pulled the plug on new “Two and a Half Men” episodes because Sheen had insulted the show’s co-creator in interviews. TV’s highest paid actor has been on a bizarre media-a-thon, ultimately causing his publicist Stan Rosenfield to quit. Sheen-isms have become a hit on the web.

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By evening, Sheen took to his own web production, Sheen's Korner. He used the live Ustream broadcast to voice his discontent with the show's executives. "Now that I have your lazy f***ing attention world, sit back and rejoice. For the Malibu Messiah, the Condor of Calabasas, the f***ing warlock of the jealous face that is before you," ranted Sheen.

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One third of Charlie Sheen's heart went missing Friday when Rachel Oberlin, one of the actor/warlock's two "goddesses," "left the building," Sheen tweeted Friday. Just hours later, Charlie told People the wayward goddess was back at Sober Valley Ranch.

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Charlie Sheen is adding another "win" to his record. The actor is reportedly in contract to buy a two-story, six-bedroom Mediterranean mansion located on a half-acre of land. Perhaps he's making room for more goddesses?

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A week into Charlie Sheen's continuing "media tsunami," actor Russell Brand sent the star a text message expressing his support. Brand follows the lead of both Mel Gibson and Sean Penn, who have been reaching out to Sheen for some time. Sheen described Gibson as "a stone cold dude" and Brand as "a b*tchin' dude."

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Getty
In a new interview on Philadelphia's Wired 96.5 The Chio & Shila Show, Sheen replied to his critic with, "To the haters, I don't speak to them anymore, I speak past them... I don't have any interest being sucked into the mire of their stupidity."

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Wired 96.5
Sheen called the Philly radio station after an airplane dragging this banner flew over his house.

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Twitter, http://twitter.com/BreeOlson
In the same interview, Sheen said of his goddesses, "they have a magical presence that makes me feel alive and focused," and "they make my blood boil like a microwave on meth." This photo is of 24-year-old "goddess" Rachel Oberlin, also known as Bree Olsen.

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Denise Richards, Sheen's second ex-wife, is "disgusted" with Sheen's behavior and wants to keep her two daughters, 6-year old Sam and 5-year old Lola, away from him.

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RadarOnline.com / AP
Earlier, cops removed his 2-year-old twin sons, Bob and Max, on a court order filed by Sheen's third wife, Brooke Mueller. Sheen allegedly threatened her by saying, "I will cut your head off, put it in a box and send it to your mom!"

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Amidst his media blitz, Sheen decided to embrace Twitter. Within 24 hours, the star's site boasted more than 600,000 followers. Under his bio, he wrote "Winning… Bring it..! (unemployed winner…)"

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Embracing his new found Twitter stardom, Sheen recently tweeted a photo of himself with a cake that portrays the Academy Award figure as … Charlie Sheen, of course. "Oscars should be called Charlies" he tweeted.

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Charlie's Hollywood Hills mansion is "a hundred thousand times better than what's going to be delivered or offered in [Brooke's] house," he told NBC News. He is currently living with two blondes he refers to as his "goddesses" -- model Natalie "Natty" Kenly and former porn star Rachel Oberlin, pictured here.

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AP
Sheen told NBC’s “Today” show he was cured of alcohol and drug addiction and ready to go back to work. But he demanded “3 mill’ an episode” instead of the $2 million he now makes. "I'm tired of pretending I'm not special," Sheen said, adding people “can't process me with a normal brain."

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AP
Sheen's off-screen life has long been a rocky road but until recently bosses had praised his professionalism. That all changed when Sheen called into the Dan Patrick Show on Feb. 14. He said “Two and a Half Men” executive producer Chuck Lorre was an ungrateful "charlatan" whose "unevolved mind" couldn’t process his fast recovery.

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AP
After increasing reports of Sheen's hard partying and hospitalizations, Lorre (l) took "Two and a Half Men" on hiatus for a month so its star could seek rehab. Lorre later joked about Sheen’s longevity in a vanity card, which apparently set the actor off.

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WireImage
Charlie Sheen was recently granted a divorce from his long-estranged third wife Brooke Mueller. The divorce ended a brief, stormy marriage that collapsed after a violent quarrel on Christmas Day 2009. Sheen won't officially be single until May 2, however, six months after the first petition was filed.

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Before Sheen's third stint in rehab in 12 months, he last made news for filing a lawsuit against Capri Anderson, the porn star found in his hotel room at the Plaza in New York City on October 25. After a boozed-up rampage, Sheen was removed from his room via ambulance.

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Sheen filed the suit after Anderson sat down for interviews with "Good Morning America" and "Nightline" in which she said she was planning to sue the actor for battery and false imprisonment.

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Cops who responded to reports of a disturbance at the Plaza Hotel found a drunken and reportedly naked Sheen and called for an ambulance at 2:07 a.m. Sheen was close to being charged with disorderly conduct, but agreed to get into the ambulance and be taken to New York Hospital. Because he agreed to be transported, Sheen was not charged with a crime.

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The Golden Globe-winning actor, who's been plagued by drug addiction and domestic-violence accusations, was in the city with ex-wife Denise Richards to promote Richards' new series "Blue Mountain State." Richards, who was staying in a separate room in the hotel, accompanied Sheen to the hospital.

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In August, Sheen pleaded guilty to a misdemeanor assault charge and was sentenced to 30 days in a rehab center, 30 days probation and 36 hours of anger management. Prosecutors dropped two more serious charges, including a felony, related to a Christmas day attack on his wife Brooke Mueller.

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Sheen, 44, was arrested on Christmas Day after his wife, Brooke Mueller, told cops in Aspen he threatened her with a knife at their vacation home.

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The sentence, which did not include any jail time, allowed Sheen to return to the set of his popular sitcom.

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AP
An earlier deal that would have had the Two and a Half Men star serve a short jail term fell apart in June. Under that deal, Sheen would have served 30 days in Aspen's jail, but work by day as an intern at the town's community theater group.

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Aspen Police Dept.
This police mug shot, provided by the Aspen Police Department, was shot immediately after Sheen's arrest. He was booked under his birth name, Carlos Irwin Estevez.

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flickr.com/ southbeachcars / Phillip Pessar
Sheen, who agreed to return to the CBS hit Two and a Half Men, was initially charged with second degree assault and menacing in the Christmas Day incident.

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CBS / AP
“To put a fitting end on the two and one-half months of whirlwind speculation, I’m looking forward to returning to my CBS home on Monday nights,” Sheen said when he returned to the show at a reported $1.8 million per episode.

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The actor initially denied the charges after his arrest. He was released after posting an $8,500 bond, then later appeared in court for formal charges on Feb. 8.

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Miss Universe Organization
Mueller called 911 on Christmas and said, "My husband had me with a knife and I feared for my life and he threatened me." Mueller has since reconciled with Sheen and wanted prosecutors to drop the case, her lawyer has said.

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Sheen, born Carlos Irwin Estevez, is the son of actor Martin Sheen and little brother of Brat Packer Emilio Estevez.

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MGM
His first major role was in 1984's Red Dawn, in which he co-starred with Jennifer Grey and Patrick Swayze. In the movie, a group of teenagers defends their Midwestern town against the invasion of foreign troops.

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Orion Pictures
The actor truly broke out in 1986's Platoon, which garnered critical and commercial success. The film won four Oscars, including Best Picture and Best Director for Oliver Stone.

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WireImage
QUOTABLE: "Fame is empowering. My mistake was that I thought I would instinctively know how to handle it."

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Paramount Pictures
Sheen worked with Jennifer Grey again when he had a small cameo in 1986's Ferris Bueller's Day Off. He played a stoner who gives Grey's character advice about her life. Sheen later attended rehab to deal with his real-life drug addiction.

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Twentieth Century-Fox
The following year, Sheen was lauded for his role as stockbroker Bud Fox in Wall Street. The film cemented his position in Hollywood.

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Twentieth Century-Fox
Charlie starred with his brother Emilio Estevez in the Brat Pack-laden movie Young Guns in 1988.

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Paramount Pictures
Sheen took a comedic turn in 1989's Major League. The film spawned two sequels, neither of which had the success of the original.

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Twentieth Century-Fox
Charlie continued in the comedic vein in the early '90s with Hot Shots! and its sequel Hot Shots! Part Deux. The movies spoofed Top Gun and Rambo respectively.

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WireImage
Sheen's professional career continued to shine. In 1994, he was honored with a star on the Hollywood Walk of Fame.

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WireImage
While his star was rising, Sheen's personal life was starting to become precarious. In 1990, he was engaged to Kelly Preston, who was accidentally shot in the actor's home. Sheen told Playboy that he wasn't even in the room, but the relationship fell apart nonetheless. Preston soon started dating John Travolta, whom she later married.

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Getty Images
After he split with Preston, Charlie dated a string of ladies outside the mainstream. In the early '90s, he was spotted with adult film star Heather Hunter.

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WireImage
He later moved on to porn star Ginger Lynn, whom he dated for an extended period in the late '90s.

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Charlie's sexual antics became public knowledge in 1994 when he was named as one of "Hollywood Madam" Heidi Fleiss' customers. He testified that he'd ordered call girls from Fleiss at least 27 times and spent about $50,000.

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In 1995, Sheen settled down and married model Donna Peele after a six-week romance. The couple divorced less than a year later.

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In 1997, Sheen pleaded no contest to criminal charges after being accused by his ex-girlfriend Brittany Ashland of domestic abuse. Ashland alleged that Sheen grabbed her hair and threw her face-first into the marble kitchen floor, splitting her lip and causing her to need seven stitches.

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In 1998, Sheen violated his probation from the previous year's battery charges by using illegal drugs. His father, Martin, turned him into police. Charlie went to rehab as part of his extended probation.

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AP
QUOTABLE: "When I was in camp and had to wear the Lo-Jack ankle bracelet monitor, I vowed there and then that I would never again do anything to lose my freedom."

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USA Films
After straightening out his personal life through rehab, Sheen's career took off again. He played himself in 1999's Being John Malkovich.

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ABC
After Michael J. Fox's departure from ABC's Spin City, Sheen stepped in as Charlie Crawford, the deputy mayor of New York. Sheen played the role for two seasons through the series' finale.

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Getty Images
In 2002, Sheen won a Golden Globe for his Spin City performance. He met Denise Richards the previous year while filming Good Advice.

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Brady Altschiller
In June 2002, Richards and Sheen married. Richards filed for divorce in March 2005 while pregnant with their second daughter, Lola. The pair officially divorced the following year.

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Jennifer Jurgrau
The divorce was accompanied by a bitter custody battle over their two daughters Samantha and Lola. Richards claimed Sheen was abusive to her and negligent to their children, and she filed a restraining order claiming he tried to kill her. Sheen denied all allegations.

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CBS
Since 2003, Sheen has starred in CBS's Two and a Half Men and has garnered four Emmy nominations and two Golden Globe nominations for the role. He's one of the nation's highest paid TV actors, and his show's ratings did not take a hit after his most recent run-in with the law.

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WireImage
In May 2008, Sheen married Brooke Mueller and the couple had twin boys in March 2009.

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KNBC
Both Sheen and Mueller, 32, entered substance abuse rehabilitation several weeks after the incident.

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AP
Sheen's off-screen life has long been a rocky road but until recently bosses had praised his professionalism. That all changed when Sheen called into the Dan Patrick Show on Feb. 14. He called “Two and a Half Men” producer Chuck Lorre an ungrateful "charlatan" whose "unevolved mind" couldn’t process his fast recovery.